Cesium carbonate → HCID 58476654, compound

HRID 2388018Notes

Reaction equation

HRID 2388018 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:10][N:11]([CH3:15])[CH2:12][C:13]#[CH:14].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[CH3:10][N:11]([CH3:15])[CH2:12][C:13]#[C:14][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([F:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 81643N,N-DimethylpropargylamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 177501445-Bromo-2-fluoropyridin-3-amine

Product 1

HCID 58476654HCID 58476654, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromo-2-fluoropyridin-3-amine (1.00 g, 5.24 mmol), N,N-dimethylprop-2-yn-1-amine (0.68 mL, 6.28 mmol), and cesium carbonate (3.41 g, 10.5 mmol) in DMF (25 mL) was degassed with argon for 15 min. To this slurry were added bis(acetonitrile)palladium(II) chloride (0.068 g, 0.26 mmol) and Xphos (0.324 g, 0.68 mmol). The suspension was allowed to stir at 50° C. for 4 h under an atmosphere of nitrogen and was then concentrated. The residue was purified by column chromatography to give 5-[3-(dimethylamino)prop-1-yn-1-yl]-2-fluoropyridin-3-amine (0.46 g, 45%).

Workup

  1. customwas degassed with argon for 15 min
  2. concentrationwas then concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ae2b7be9098e42e2aad78e5bb29b8995
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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